# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1059467'
_audit_update_record             
;
2015-04-14 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 N4 O3'
_chemical_formula_sum            'C11 H8 N4 O3'
_chemical_formula_weight         244.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.5740(13)
_cell_length_b                   22.414(5)
_cell_length_c                   7.9769(16)
_cell_angle_alpha                90
_cell_angle_beta                 113.126(4)
_cell_angle_gamma                90
_cell_volume                     1080.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    179
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12165
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.817
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2625
_reflns_number_gt                1671
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0890(3) 0.26456(8) -0.1618(3) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.3891(3) 0.21349(7) -0.1658(2) 0.0261(4) Uani 1 1 d . . . . .
O3 O 0.5521(3) 0.02003(7) 0.3256(2) 0.0226(4) Uani 1 1 d . . . . .
N1 N 0.2165(3) 0.22198(9) -0.0983(3) 0.0226(5) Uani 1 1 d . . . . .
N2 N 0.5077(3) 0.16381(9) -0.0809(3) 0.0227(5) Uani 1 1 d . . . . .
N3 N 0.4223(3) 0.07109(9) 0.2521(3) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.6762(3) 0.05842(9) 0.1278(3) 0.0185(4) Uani 1 1 d . . . . .
C1 C 0.2351(4) 0.17978(10) 0.0214(3) 0.0196(5) Uani 1 1 d . . . . .
C1A C 0.0892(4) 0.17734(12) 0.1225(4) 0.0279(6) Uani 1 1 d . . . . .
H1AA H -0.0428 0.2017 0.0595 0.042 Uiso 1 1 calc R U . . .
H1AB H 0.1685 0.1928 0.2461 0.042 Uiso 1 1 calc R U . . .
H1AC H 0.0451 0.1359 0.1290 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4170(4) 0.14446(10) 0.0287(3) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.5056(3) 0.09094(10) 0.1387(3) 0.0158(5) Uani 1 1 d . . . . .
C4 C 0.6969(4) 0.01588(10) 0.2458(3) 0.0172(5) Uani 1 1 d . . . . .
C5 C 0.8537(4) -0.03369(10) 0.2948(3) 0.0179(5) Uani 1 1 d . . . . .
C6 C 1.0141(4) -0.03447(10) 0.2219(3) 0.0201(5) Uani 1 1 d . . . . .
H6A H 1.0213 -0.0029 0.1451 0.024 Uiso 1 1 calc R U . . .
C7 C 1.1633(4) -0.08114(11) 0.2609(3) 0.0222(5) Uani 1 1 d . . . . .
H7A H 1.2709 -0.0820 0.2090 0.027 Uiso 1 1 calc R U . . .
C8 C 1.1551(4) -0.12668(11) 0.3761(3) 0.0244(6) Uani 1 1 d . . . . .
H8A H 1.2574 -0.1588 0.4030 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9980(4) -0.12538(11) 0.4518(3) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.9946 -0.1563 0.5321 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8456(4) -0.07914(11) 0.4110(3) 0.0219(5) Uani 1 1 d . . . . .
H10A H 0.7369 -0.0785 0.4619 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.239(2) . ?
O2 N2 1.376(2) . ?
O2 N1 1.447(3) . ?
O3 C4 1.340(3) . ?
O3 N3 1.410(2) . ?
N1 C1 1.315(3) . ?
N2 C2 1.310(3) . ?
N3 C3 1.306(3) . ?
N4 C4 1.309(3) . ?
N4 C3 1.369(3) . ?
C1 C2 1.416(3) . ?
C1 C1A 1.477(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2 C3 1.465(3) . ?
C4 C5 1.461(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.392(3) . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 N1 107.36(16) . . ?
C4 O3 N3 106.58(17) . . ?
O1 N1 C1 134.9(2) . . ?
O1 N1 O2 116.86(19) . . ?
C1 N1 O2 108.23(18) . . ?
C2 N2 O2 106.16(19) . . ?
C3 N3 O3 102.41(18) . . ?
C4 N4 C3 101.45(19) . . ?
N1 C1 C2 105.6(2) . . ?
N1 C1 C1A 121.9(2) . . ?
C2 C1 C1A 132.5(2) . . ?
C1 C1A H1AA 109.5 . . ?
C1 C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C1 C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N2 C2 C1 112.7(2) . . ?
N2 C2 C3 119.5(2) . . ?
C1 C2 C3 127.8(2) . . ?
N3 C3 N4 116.1(2) . . ?
N3 C3 C2 121.2(2) . . ?
N4 C3 C2 122.7(2) . . ?
N4 C4 O3 113.5(2) . . ?
N4 C4 C5 127.6(2) . . ?
O3 C4 C5 118.9(2) . . ?
C6 C5 C10 120.2(2) . . ?
C6 C5 C4 118.0(2) . . ?
C10 C5 C4 121.8(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C5 119.3(2) . . ?
C9 C10 H10A 120.4 . . ?
C5 C10 H10A 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 O2 N1 O1 -178.97(18) . . . . ?
N2 O2 N1 C1 0.6(2) . . . . ?
N1 O2 N2 C2 -0.5(2) . . . . ?
C4 O3 N3 C3 -0.1(2) . . . . ?
O1 N1 C1 C2 179.0(2) . . . . ?
O2 N1 C1 C2 -0.5(2) . . . . ?
O1 N1 C1 C1A -3.3(4) . . . . ?
O2 N1 C1 C1A 177.19(19) . . . . ?
O2 N2 C2 C1 0.3(3) . . . . ?
O2 N2 C2 C3 179.36(18) . . . . ?
N1 C1 C2 N2 0.1(3) . . . . ?
C1A C1 C2 N2 -177.1(2) . . . . ?
N1 C1 C2 C3 -178.9(2) . . . . ?
C1A C1 C2 C3 3.8(4) . . . . ?
O3 N3 C3 N4 0.4(2) . . . . ?
O3 N3 C3 C2 179.46(18) . . . . ?
C4 N4 C3 N3 -0.5(3) . . . . ?
C4 N4 C3 C2 -179.5(2) . . . . ?
N2 C2 C3 N3 178.6(2) . . . . ?
C1 C2 C3 N3 -2.5(3) . . . . ?
N2 C2 C3 N4 -2.4(3) . . . . ?
C1 C2 C3 N4 176.5(2) . . . . ?
C3 N4 C4 O3 0.4(2) . . . . ?
C3 N4 C4 C5 179.6(2) . . . . ?
N3 O3 C4 N4 -0.2(2) . . . . ?
N3 O3 C4 C5 -179.50(18) . . . . ?
N4 C4 C5 C6 6.0(3) . . . . ?
O3 C4 C5 C6 -174.8(2) . . . . ?
N4 C4 C5 C10 -174.1(2) . . . . ?
O3 C4 C5 C10 5.1(3) . . . . ?
C10 C5 C6 C7 1.6(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C6 C5 C10 C9 -0.6(3) . . . . ?
C4 C5 C10 C9 179.6(2) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059

_shelxl_version_number           2014/6

